


Pennywise's Whorehouse

by BasementVampire



Series: The Whorehouse Series [2]
Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Anal Sex, Crack, Daddy Kink, Emetophilia, Humor, Incest, M/M, Oral Sex, Parody, Prostitution, Richie Tozier Has a Big Dick, Richie and Eddie fuck a LOT, Smut, Unsafe Sex, Vomiting, bill is an absolute simp for stan, eddie wears a fanny pack while getting fucked, finding love in a whorehouse, mike locked the door on his parents, this was supposed to be crack but i took it a little too seriously lmao, woundfucking
Language: English
Status: Completed
Published: 2020-04-14
Updated: 2020-04-14
Packaged: 2021-03-02 02:06:41
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 5,091
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23657320
Author URL: https://archiveofourown.org/users/BasementVampire/pseuds/BasementVampire
Summary: Bill gets a job at the most exclusive whorehouse in Derry and ends up finding love along the way...(PLEASE read the tags/trigger warnings!)
Relationships: Alvin Marsh/Beverly Marsh, Bill Denbrough/Pennywise, Bill Denbrough/Stanley Uris, Eddie Kaspbrak/Richie Tozier
Series: The Whorehouse Series [2]
Series URL: https://archiveofourown.org/series/2094246
Comments: 15
Kudos: 36





	Pennywise's Whorehouse

**Author's Note:**

  * Inspired by [Pimps and Bitches](https://archiveofourown.org/works/495111) by [orphan_account](https://archiveofourown.org/users/orphan_account/pseuds/orphan_account). 



> Hello all! I am the author of literary masterpiece "Squip's Whorehouse" and I am back at it again with the tale of Pennywise's whorehouse. This is a joke so please don't take it too seriously. It was inspired by "Pimps and Bitches." (I'd also like to give a shoutout to the fic "I need that like I need another hole in my head" by asonyplaystation, which inspired a part of this!)
> 
> PLEASE READ: TW for rape, blood/violence, R slur, and incest  
> This is all done in good fun, but please be aware of these elements of the story! (I'd also like to point out that everyone in the story is 18+)
> 
> Anyways, without further ado, please enjoy!

Bill Denbrough had graduated high school three weeks ago and had only just realized that he was—in a word—fucked. His only aspiration in life was to read audiobooks, but he’d had his first audition yesterday and they had plainly told him he would never make it when he started with, “It w-was the best of t-t-times, it w-was the w-w-worst of t-times…”

Bill sat in his bedroom on a Saturday afternoon, wracking his brain for alternative career paths. He was scrolling through Twitter when it hit him—one of his friends had retweeted an ad for the coolest whorehouse in Derry, the _Losers Club_. It was an exclusive members-only club that boasted the finest whores in all of Maine.

 _That’s it!_ Bill thought, a light bulb going off in his head. It was the perfect job for him—he LOVED to fuck, and he was good at it, too. He could suck dick like a champ, and he had an _amazing_ ass (or so he’d been told.) He contemplated the pros and cons of the job and ultimately decided to send an email to the owner of the whorehouse, a man referred to only as “Pennywise.”

A few days later, Bill showed up at the Losers Club for his interview. He’d been informed that this meeting would not only be a discussion of his resume and career goals, but also a chance to test his skills. Bill had douched that morning, AND shaved his asshole. He was ready to blow Pennywise away (or just _blow_ him, if that was the case.)

It was two in the afternoon and the whorehouse wasn’t open yet, so Bill knocked on the back door like he’d been instructed. It opened to reveal a thin, sandy-haired boy in an oversized blue T-shirt that fell off one shoulder. Bill’s gay ass was GAGGED.

“You must be Bill,” the boy said, looking him up and down.

“Y-yeah nice to m-m-meet you,” he replied.

“Same here. I’m Stan,” he introduced himself, giving Bill THE most SALACIOUS look of his life. “Come on in, I’ll take you to Pennywise’s office.”

Bill followed Stan through the whorehouse, up a flight of stairs and down a hall until finally they reached a red wooden door. “Thanks,” Bill said, giving the other boy a tentative smile.

“Good luck,” Stan said, before turning to walk away, leaving him alone in the hall.

Bill took a deep breath, steeling himself before knocking on the door. “Come in!” a voice called from inside. Bill turned the knob, heart pounding in his chest, and swung open the door.

The office was grimy and dimly lit, and toward the back there was a desk with a spinning chair behind it, turned away from him and obscuring the whorehouse’s owner from view. All Bill could see was a shock of orange hair sticking up over the back of the chair.

“H-hi,” Bill said nervously. “I’m B-Bill Denbrough. I’m h-here for the-the interview.” He shut the door behind him.

The chair spun around suddenly to reveal Pennywise who was dressed as a FUCKING CLOWN!

“WHAT THE FUCK?!” Bill screamed, jumping back. The man had a pasty white face with big red lips, a red nose, and red lines running through his eyes and hooking into his mouth. He looked SCARY AS SHIT.

Pennywise laughed unsettlingly. “Don’t be scared, Bill. I’m Pennywise the _dancing_ clown! We all float here!”

Bill glared at him. “Okay, can you not be so weird and cryptic? What the everloving FUCK is going on?”

Pennywise’s face fell, and he continued in a totally normal human voice. “Sorry, dude. It’s just, like…you gotta do something to stand out in this world, y’know?”

“I g-get it,” Bill said with a shrug. “Y-your makeup l-looks really g-g-good.”

Pennywise grinned. “Thanks. Have a seat.” He gestured to the empty chair in front of the desk.

Bill took a seat, and they spent the next ten or so minutes talking about Bill’s previous jobs (Taco Bell and Marshall’s) and his life aspirations (he had none, but he managed to pull something out of his freshly-shaven ass.)

“Now,” Pennywise said after a lull in the conversation. “The part I’ve been looking forward to…I’m going to see if you’ve got what it takes to be a whore here at the Losers Club.” He stood from his chair and walked toward the back of the room, where a small table held a record player. Pennywise lowered the needle onto the record that was already there, and it started playing circus music.

“DA DA DADA DADA DA DA DA DA!” Pennywise started singing. He made Bill get on his knees in front of him, and Bill pulled down his billowy white clown pants, eyes widening when he realized Penny was going commando!

“W-wow your cock is s-so big, Da-Daddy,” Bill said, admiring the other man’s throbbing member. It was purple and veiny, and squirting little dollops of precum from the slit. Bill took it into his mouth, hollowing his cheeks as he lowered himself onto the other man’s erection. He looked up and saw Pennywise staring back down at him, mouth hanging open and drool pouring down his chin. He grabbed a fistful of Bill’s hair, encouraging him to suck harder and faster, moaning like a LITTLE BITCH-ASS WHORE as he let Penny fuck his throat raw.

“You’re such a good little cocksucker, Billy,” he praised, finally pushing the boy off his dick and dragging him to a bed in the corner of the room. Pennywise was waddling because he still had his pants pulled down around his ankles.

Bill stripped off his clothes in a hurry, desperate to prove himself to the owner of the whorehouse. He got on his hands and knees, wiggling his phat ass for Pennywise. The clown knelt behind him, spreading his ass treeks and admiring Bill’s fluttering pink hole.

“Did you stretch yourself for me already?” Pennywise purred, grabbing lube from out of nowhere—it was Sliquid Sassy, of course, only the best for his whores—and pouring it on his monster cock.

“Y-yes, Daddy,” Bill stammered, feeling his own dick throbbing and leaking between his legs.

Pennywise saw precum drip out of Billy’s peepee and gasped. “Juicy squirt!”

Then with no warning he RAMMED his cock into Bill. He growled and fucked him like an animal, making the boy scream with pleasure. “Oh, yeah!” Penny panted. “Who’s ur daddy!”

Like he was on a fucking hair trigger, Bill sobbed and started nutting all over the sheets. He whined when he felt Pennywise’s hot cum pump into him, painting his insides like the world’s dirtiest Twinkie, filled up to bursting with white creamy goodness.

Pennywise grinned and sat back on his haunches, catching his breath. His softening cock slipped free of Bill’s hole and he watched his nut leak out. “You start tomorrow!” he declared.

*****

Bill arrived at the whorehouse the next day with a duffel bag in his hand. Stan answered the door yet again, greeting him with a stupid gay ass grin that Bill returned like the fucking simp that he was.

“Let me give you a tour,” Stan said, taking Bill inside. He first showed him to his room, letting him set his things down. They toured the club downstairs, before returning upstairs to where the whores’ quarters and the private bedrooms were. They passed a closed door, and Bill could hear loud moaning coming from inside. Confused, since the club wasn’t open yet, he opened the door and peered into the room. Some kid with curly hair and glasses was screwing the shit out a boy Bill could only HOPE was legal. Or maybe he was just a baby face twink. He was naked except for a fanny pack clipped around his waist.

“Oh, don’t mind them,” Stan said, waving his hand. “That’s just Eddie and Richie. They’re always fucking even though they know they’re noT SUPPOSED TO DO THAT, CUZ THEY’RE SUPPOSED TO SAVE THEMSELVES FOR PAYING CUSTOMERS!” He shouted the last part so the other boys could hear him.

“Fuck off, Urine!” the curly-haired boy yelled back, not bothering to look toward the door as he flipped Stanley off.

Bill shut the door politely, following Stan further down the hall and into a brightly lit room.

“This is the break room,” Stan explained. There were a few couches covered in questionable stains, a mini fridge and a water cooler, and a table. Bill took it all in, barely noticing the people in the room until Stan said, “Let me introduce you to the other whores. Everyone, this is Bill. He’s the newest whore here. Alright. This is Ben…” He pointed to a chubby dude chilling on one of the couches. “He’ll serenade you with New Kids on the Block if you ask nicely.”

“Sup, noob,” he replied, nodding once in Bill’s direction.

“That’s Mike, he’s a pyromaniac.”

Mike looked up from the book he was reading to see Stan pointing at him and Bill staring like a stupid goldfish. “Don’t piss me off. My parents made that mistake…”

Bill’s eyes widened and he glanced over at Stan, but Stan was not paying attention in the least, already moving on the the next introduction like nothing had happened. “Bev here is the only girl in the whorehouse. She has a blood kink.”

The cute redheaded girl gave a little wave. At that moment, a disheveled Richie and Eddie burst into the room, laughing and grinning. “What’s up, losers?” Richie said, looking around the room before locking eyes with Bill, giving him a smirk.

Stan sighed as if it pained him to introduce the other boy. “This is Richie—”

“Richie Trashmouth Tozier, at your service,” Richie said with an overdramatic bow. “Biggest dick in the whorehouse!”

Stan stared at him and deadpanned, “Big dick doesn’t count if half of it is your personality.”

Richie continued as if he hadn’t heard. “This is Eddie Spaghetti.” He leaned in toward Bill and dropped his voice to a mock whisper. “ _He used to be a heroine addict, before he moved to Africa._ ”

“ _Hey_ , you don’t need to tell people that,” Eddie sputtered.

“And this,” Richie continued, waving his hand toward Stan with a flourish, “is Stan the Man. He has the tip of his dick sliced off.”

“It’s called being circumcised, asshole.”

“N-nice to m-meet you all,” Bill said. “I think I’m g-g-gonna go sh-shower before we open for t-the night.”

“I’ll walk you to your room,” Stan offered.

Once there, Stan followed Bill in, shutting the door behind them. “So…are we gonna fuck or what?”

Bill turned redder than a baby’s bottom after a birthday spanking. “Is-is that a-allowed?”

“Are you gonna tell Pennyboi?” Stan countered.

“N-no,” Bill said with a smile, feeling warm at the thought of sharing a secret. It reminded him of when he and Georgie were kids, huddled together under a blanket and illuminated by the cozy glow of a flashlight, reading aloud from fantasy books. All hushed voices and muffled laughter and the smell of pages turning.

Bill broke out of his mawkish reverie to find Stan whipping his dick out.

*****

Richie and Eddie had snuck away to one of the private rooms again, and yes, it had only been, like, twenty minutes since they’d fucked, but they were like, 18 or 19, or some age that was legal but still young enough to be a nymphomaniac. And their dumb asses were horny as FUCK.

Eddie was lying back on the bed, watching as Richie jerk off over his bare stomach. “Mmmm yes,” he moaned, “I want your sauce on my Eddie Spaghetti.”

His boyfriend’s smoldering words, paired with the cocktail of hormones raving inside him like squirrels on speed (or did he forget his Adderall that morning?), sent Richie over the edge. He moaned, spilling his Richie Sauce all over the other boy’s chest and tummy. He panted, reaching down to rub it into Eddie’s skin with his hand.

“Fuck you’re so hot,” Richie breathed, scooting down the bed between the other’s legs. “I wanna make you come so bad.” And he wanted to try something they’d never done before…

Eddie’s hand tangled in Richie’s hair, guiding him to his hard cock. But wait! Richie was going somewhere else…he was licking Eddie’s asshole!!

Eddie shrieked, trying to pull on his boyfriend’s hair, but Richie didn’t let up. He licked wet stripes over Eddie’s hole, dipping his tongue in and tasting sweat and skin.

“Richie!” Eddie screamed indignantly, smacking the side of Richie’s head. “Stop it, that’s _so_ gross!”

“You taste so good,” Richie said, nipping at the inside of Eddie’s thigh.

“ _Ugh_ , I do not _taste good_ ,” Eddie spluttered. God, there must be so many germs transferring from his ass to his boyfriend’s mouth. “It tastes like ASS.”

But even though Eddie was being a pussy ass little bitch about it, getting his ass ate felt REALLY GOOD. With Richie jerking him off at the same time, he came all over himself.

Smiling like an idiot, Richie leaned over him and kissed Eddie heatedly, licking into his mouth. Eddie yelped, shoving the other boy back in horror.

“Oh my— _BLEEEECH!_ ” Eddie turned his head and puked onto the floor. It splattered on the ground with a wet noise.

Suddenly Richie had a FUCKING spasm and nutted instantly, for a second time. He had a BIG vomit kink.

*****

After getting fucked within an inch of his own life by Stan, and then showering like he’d originally planned, Bill had been called to Pennywise’s office for training before he was to meet with clients. Bill slipped into something more comfortable—a silk lilac button down open over his bare chest and black sweatpants. Sophisticated, yet slutty. Perfect.

Oh, and of course he wasn’t wearing underwear.

Bill knocked hesitantly on the door, heart pounding for reasons he couldn’t quite explain. He didn’t know what it was, but something about Pennywise just made him feel…warm. Safe. Yet nervous, like a pregnant mother with the world’s tiniest vagina about to give birth to her first child.

“Hello, Billy,” Penny singsong-ed upon opening the door. He smiled down at his newest whore, inviting him into the room. He was still dressed like some kind of freaky sewer clown, but somehow, Bill found it endearing.

“Hi, D-Daddy,” Bill said, suddenly tongue-tied. What had gotten into him? “W-What did you have in m-mind for our training today?”

Pennywise smiled, shutting the door behind them and leading Bill to the bed in the back of the room. “Well, today I am going to test your self control. Unfortunately, clients won’t always let you enjoy yourself during your sessions. So today I am going to fuck you, and you will not be allowed to cum. Understand?”

“Y-Yes, Daddy,” Bill replied dutifully, even though he was disappointed.

Pennywise pulled down his pants enough to get his dick out and sat back against the headboard. “Ride me,” he ordered, watching, entranced as Bill hovered over his cock. He didn’t know why he suddenly felt like he was burning up from the inside out, heart beating out of control like it was going to burst out of his sexy, toned chest at any second. It couldn’t be Billy that was making him feel this way, surely? He was just the merchandise—there was no reason a simple whore should be riling Penny up like a twelve-year-old boy who had just discovered tickling his pickle.

“D-Daddy? You seem a little d-distracted,” Bill said. He was poised over Pennywise’s dick, letting the head rub against him and smear precum on his asshole.

“Sorry,” Pennywise said. He grabbed onto the boy’s hips and pulled him down onto his cock, fucking up into him with all the force of a chimpanzee high off Xanax.

Bill whined, letting Penny use him while his own hard dick leaked onto the man’s white clown shirt. Finally, Pennywise came with a roar, shooting his hot nut into Bill and breeding him.

“Daddy,” he whimpered, but Pennywise pushed him off his lap and shooed him out the door.

“Go take care of yourself,” he ordered, and Bill pulled his pants up as he scurried out the door.

*****

When Bill got back to his room, he was in such a hurry to nut off that he didn’t remember to lock his door. He was sitting on his bed, pants off and silk shirt falling artfully off his shoulders. He was a picture of sin, hand fisting his cock as he tried not to think about Pennywise—about that fiery hair, that beautifully pale face intersected with blood red, his lilting, playful voice…

NO! Bill couldn’t be having these thoughts—Penny was his BOSS! And he, nothing but a mere whore.

His conflicted inner monologue was suddenly interrupted by the door being flung open, as Mike and Ben burst into the room. Before Bill could so much as cover himself or even ask what they were doing, the two boys were on him, pinning him face-down to the bed.

“You think you can just come in here and be the favorite?!” Mike yelled, holding Bill down as he struggled. “Well, we’ll see if Pennywise still likes you once you’re damaged goods…”

“S-Stop,” Bill said weakly as hands spread his plump ass cheeks.

“Stop struggling,” Ben snapped, shoving a finger into Bill, still loose from his training with Pennywise. “You’re only making it worse for yourself.”

“I bet you could get your whole hand in that slutty hole,” Mike said with a dark laugh, slapping that big ol’ booty.

Ben forced the rest of his fingers into Bill’s ass, making him SCREAM, while Mike moved down to the bottom of the bed to caress Bill’s foot. He started licking it sensually, sucking the little one into his mouth. “MMM tasty pinkie toe!” Mike said.

Bill yelped and squirmed as Ben fisted him, shoving his whole hand up in those guts. He was ashamed that his dick was still hard and wet where it was trapped between his stomach and the bed.

“Mike, see if you can get your hand in here, too,” Ben ordered. Mike started pushing his fingers into Bill and once both boys had a hand inside, they thrust them in and out and spread them apart, slicked up with blood for lube.

“Stop, p-please!” Bill begged. He didn’t know why these boys hated him so much, but all he wanted was for his Daddy to come and save him. Why had he even come here? He didn’t belong, this was a terrible idea…

“Stop r-raping me,” Bill whimpered.

Mike smacked the back of his head. “Just consent and it won’t be rape anymore!”

“Rape is n-not a j-j-joke,” Bill said.

“If only the author knew that,” Ben said with a shrug.

“The what?” Mike asked.

“Nothing. Come on, let’s ruin this bitch.” He started singing “Baby I Believe in You” as they double fisted him with no lube.

*****

Eddie was furiously brushing his teeth. For the third time.

He had kind of blacked out after everything that happened, but when he woke up to Richie sitting by his side and remembered what happened, he ran to the bathroom to clean up.

“Babe, I’m sorry…” Richie started, trailing behind his boyfriend.

“Do NOT follow me,” Eddie demanded.

Richie left to go to the break room and get a snack, maybe fuck with Stan, maybe FUCK Stan…who knew? The night was young.

Now, Eddie was spitting into the sink and stashing his toothbrush and toothpaste in the medicine cabinet (he had a toothbrush and toothpaste hidden in every bathroom in the whorehouse, for emergencies.)

When Eddie lifted his head up, suddenly he saw that bitch Henry Bowers in the mirror behind him! Bowers grinned evilly like a little goblin and stabbed him deadass in the cheek!!!!!

Eddie screamed, turning around and grabbing at his face. But before Bowers could advance any further, Pennywise sprang through the doorway and drove a knife into his neck repeatedly.

“What the fuck…” Eddie whispered, white as a ghost. White as a sheet. White as a guy named Justin at a Nickelback concert.

Penny slung the lifeless body over his shoulder with ease. “We all float down here!” he hooted. Then he took the body back to his office to cannibalize, as he sometimes did.

*****

Bev went to the private room where her next customer was waiting and when she opened the door—her DAD???

“Hey Bevvie,” he said like a creepy pedophile—like the cracker R. Kelly. Bev dad took off he gotdamn jens. “Be a good little girl and join me on the bed.”

Bev shook her head. “No, what the fuck?”

He glared at her. “Um excuse me I paid good money for you. Do you really want to make Pennywise mad?”

“I guess not.” Bev climbed into bed with him. She pulled up her white dress and he stuck his dick in her without a CONDOMMMMM that dumb fuck.

“Yes your mother didn’t fuck good like this!” he said and then pulled out a bottle a perfume and squirted her with it.

“Ah yes give it to me Daddy!” she cried. The bed slammed back and forth against the wall from how hard her dad was fucking her.

Suddenly he punched her—as he always did when he nutted—but wait!! He wasn’t wearing protection!

Bev screamed. “Daddy what the fuck?! You’re gonna get me PREGNANT!!!”

He pulled out and started putting his jeans back on without a second thought to giving his only daughter—his FLESH AND BLOOD—a creampie. “Oh well,” he said. “I guess you’ll have to raise a retard baby. It’s not hard, I did it for 18 years!” He smiled and left.

*****

Richie left the break room after grabbing a snack. No one else was there for him to annoy so he decided to go back to find Eddie. When he entered the bedroom it appeared to be empty, but upon looking around, he spotted his boyfriend slumped against the far wall, holding a towel to his face. It was white but soaked red with blood.

“Holy shit! Eds!” Richie yelled, rushing over to him. He knelt on the ground next to the other boy, staring at him in horror. “What the fuck happened to you?”

Eddie looked up at him with these big, pretty doe eyes, and Richie wished he could drown in them. Eddie was so soft but so strong, like a hurricane hiding behind a summer shower. He said, “I got stabbed in the fuckin face, you moron. What’s it look like happened to me?”

“Thought you might’ve popped a blood vessel when you found out I fucked your mom,” Richie shot back.

“Haha, very funny dickwad,” Eddie said, and a bit of blood trickled out of his mouth. “No, for real though. Bowers was here and stuck a knife clean through my face.”

“Oh, shit. Lemme see.” Richie pulled the other boy’s hand aside, uncovering the wound. He reached up gingerly to touch it, tracing the edge of raised skin with a finger. Without thinking, he dipped it into the wound, pulling back when it made Eddie hiss in pain.

“Shit, sorry,” he muttered. He wasn’t that sorry.

Eddie grabbed him by the shirt and pulled him closer so they were face to face. With a glare set in his jaw, he gritted out, “Stop threatening to hurt me if you’re not gonna hurt me. You know I like physical contact and you know when you hurt me I like it. So just start doing it.”

“I’m sorry I don’t wanna tempt you. I do wanna—I don’t…”

Eddie pulled him back in when he leaned away. “Your breath smells like coffee bean.”

Hesitantly, Richie touched the hole in Eddie’s cheek. “You get dropped on your head as a baby or something, Spaghetti?”

Eddie made a noise a little like a three-legged mouse about to be devoured by its mother when Richie’s finger poked through to the inside of his mouth. It touched his teeth and Eddie ran his tongue over it.

“Fdsukclj sdkjs,” he tried, garbled by the intrusion in his mouth.

“What?” Richie asked, pulling his finger out of the other boy’s face. It was covered in blood.

“Fuck my face.”

“Um. Fucking PARDON?” Richie said. Eddie could NOT be saying what Richie thought he was saying.

Eddie stared at him like he was a dumbass (he _was_ but that’s neither here nor there.) “I want you to put your dick through the hole in my face and fuck me. Or should I get your sister to do it instead?”

Richie shook his head, but he was smirking. “I’ll do it if you stop being a brat. But then I’m taking you to the FUCKING hospital.”

*****

Bill was lying in bed crying when Stan came into his room. “Bill?” he said. “What’s going on?”

Bill sniffed, looking up at Stan with red eyes, tear stains carved into his cheeks. “M-Mike and Ben…t-they…they r-raped me.”

Stan climbed into bed next to him and pulled Bill into his arms. “Fuck, Bill. I’m so sorry.”

“They s-said they were j-j-jealous of me. T-That D-Daddy Pennywise liked m-me more than them,” Bill sobbed.

With a hand under the other boy’s chin, Stan gently tilted his head up. “Bill, look at me. You will get past this. I know it seems unbearable and all-consuming right now, but trust me, things will get better. You are not defined by your trauma.”

Bill gave him a watery smile. “Thanks, Stan. I d-don’t d-deserve you.”

“I think you should tell Pennyboi what happened,” Stan said.

Bill frowned. “N-No, I don’t want to b-bother him. I’m just o-one of his whores, w-why would he c-care?”

“He cares about you a lot more than you know.” Stan brushed a stray lock of hair off Bill’s forehead. “And I know you care about him, too, even though neither of you will admit it. So I think you should go see him.”

“You r-really think so?”

“Absolutely.”

Stan helped him clean up and get dressed, then kissed him chastely before sending him off to Pennywise’s office. When Bill reached that looming red door, he took a deep breath, steeled himself, and knocked. When the door swung open and Bill met Penny’s honey yellow eyes, it took everything in him not to burst into tears.

“Back so soon, Billy?” Penny said. He was out of his clown garb, dressed in a simple cream colored shirt and black pants with suspenders. His hair—his real hair—was brownish blond and parted in the middle. Bill wanted to run his fingers through it.

“H-Hi, Daddy,” Bill said. “Can I c-come in? I n-need to t-talk to you.”

“Of course,” Pennywise replied, beckoning him into the office. They sat together on the bed, knees barely touching, and Bill wrung his hands.

“Daddy, s-something happened, p-please don’t b-be mad…”

“What is it Billy boy?”

Bill pursed his lips. Something about Pennywise made him feel unbridled and disarmed. He continued with more confidence. “Mike and B-Ben. They…r-raped me.”

Penny gasped softly. “Billy…no…”

Bill looked up at him imploringly. “I’m s-sorry.”

“That’s not your fault, Bill,” Penny cooed, petting the boy’s hair. “What happened?”

“They s-said they were m-mad because you-you care ab-bout me. Is t-that true?”

Pennywise looked at him with LITERAL heart eyes. He was burning—the splendid, silent sun with all his beams full-dazzling. “I…I think I love you.”

Bill gaped at him like a guppy. “R-Really? I l-love you too.”

Then they made out RIGHT THERE and they’re tongue battled for dominance!

“Daddy,” Bill murmured. “I n-need you…”

They shuffled out of their clothes like two suitcases tumbling down a conveyor belt, and Penny rolled on top of Bill, kissing down his neck.

Bill whimpered. “I-I’m still sore.”

Penny nodded contemplatively. “I…I will let you top.”

Bill sucked in a breath. “A-Are you serious?”

“Of course I am, Billy boy!” Pennywise said with his signature unhinged laugh.

Bill gave him a Look™. “Could you NOT do that fucking voice?”

Penny frowned. “Sorry. I’ll talk normally.”

Then, he got on his hands and knees, after procuring the lube for Bill to use on him. Bill fingered him open carefully—he’d never topped before! Penny moaned the whole time and it gave Bill the confidence he needed to continue, slicking his cock with lube and sliding in balls deep into his Daddy Pennywise’s ass. They both moaned in unison, and there was drool dripping out of Penny’s mouth and pooling on the pillow.

Bill tipped his head back as he thrust in and out, high on endorphins and addicted to the feeling of Penny’s tight heat around his cock. And the moans Penny was letting escape his lips were so sweet—Bill wanted to bask in these ephemeral pleasures forever.

“AHHHH please nut in my ass!” Penny cried, slamming his hips back into Bill’s. “Fill me up with your hot man seed!”

With a loud groan, Bill unloaded his baby gravy into Pennywise’s rectum. At the same time, Penny creamed himself, collapsing onto the bed. They both panted as they came down, and Bill lay down next to his lover. They held each other close, savoring the afterglow.

“Bill, that was amazing,” Penny praised, fingers carding through the boy’s hair.

Bill smiled shyly. “I’m g-glad you thought s-so. I t-thought it was g-great, too.”

Pennywise sighed. “I have to take you away from here. You deserve so much more than this.”

“R-Really?” Bill breathed incredulously. “You w-want a life with m-me?”

“Of course. Let’s get dressed, and then I’ll take you to pack your things.”

They got dressed and Pennywise packed a bag with everything he needed, then he took Bill back to his room to gather his things. They were smiling the whole time and Penny rested his hand on Bill’s lower back protectively.

Stan was waiting for them in the hall, and he embraced Bill tenderly, bidding him farewell. Pennywise handed Stan the keys to the whorehouse, explaining, “I’m leaving you in charge. I trust you to take good care of things, Stanley.”

Stan smiled. “I’ll keep things running smoothly,” he promised.

Then, Bill and Penny drove off into the sunset. Where they were going, they did not know. But one thing was for sure—as long as they had each other, everything would be okay.

**Author's Note:**

> Pls give me comments and kudos I need it to feed my family


End file.
